Sulfuric Acid → HCID 86599499, compound

HRID 855124Notes

Reaction equation

HRID 855124 reaction equation
[CH2:1]([O:3][C:4]#[C:5][C:6]1[CH:7]=[C:8]([O:25][C:26]([F:29])([F:28])[F:27])[CH:9]=[C:10]2[C:15]=1[O:14][CH:13]([C:16]([F:19])([F:18])[F:17])[C:12]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:11]2)[CH3:2].[OH:30]S(O)(=O)=O.C([O-])(O)=O.[Na+].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.O>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][C:6]1[CH:7]=[C:8]([O:25][C:26]([F:27])([F:29])[F:28])[CH:9]=[C:10]2[C:15]=1[O:14][CH:13]([C:16]([F:17])([F:18])[F:19])[C:12]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:11]2)[CH3:2]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 86599498HCID 86599498, compound

Product 1

HCID 86599499HCID 86599499, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 8-(ethoxyethynyl)-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Step 2 (1.73 g, 4.08 mmole) in a mixture of acetone (32 mL) and H2O (8 mL) was treated with H2SO4 (0.800 g, 8.15 mmole) and the resulting mixture was stiffed at room temperature for 2.5 hrs. Saturated NaHCO3 (200 mL) and then solid K2CO3 were then added and the product was extracted with EtOAc (300 mL). The EtOAc solution was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by silica chromatography (0%-15% EtOAc-hexanes gradient) to give 1.47 g (82% yield) of the product as a yellow crystalline solid: EIHRMS m/z 442.0880 (M+, C18H16F6O6, Calc'd 442.0851).

Workup

  1. extractionthe product was extracted with EtOAc (300 mL)
  2. washThe EtOAc solution was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica chromatography (0%-15% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-856353cc98784a34a9a86557c00282c8
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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